L-(-)-5-acetyl-1,3,6-tri-O-benzyl-myo-inositol | 1365626-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: L-(-)-5-acetyl-1,3,6-tri-O-benzyl-myo-inositol
• 英文别名: [(1R,2S,3R,4S,5S,6R)-2,4-dihydroxy-3,5,6-tris(phenylmethoxy)cyclohexyl] acetate
• CAS: 1365626-51-2
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: GAVWYLQTWMHDGP-KLUNGUGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 在 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 甲基叔丁基醚 、 水 、 甲苯 为溶剂， 反应 126.0h， 生成 L-(-)-5-acetyl-1,3,6-tri-O-benzyl-myo-inositol 、 1D-1,3,6-tri-O-benzyl-myo-inositol
  参考文献：
  名称：

  On the kinetic resolution of sterically hindered myo-inositol derivatives in organic media by lipases

  摘要：

  Sterically hindered myo-inositol derivatives were assayed against different commercial lipases. It was found that DL-1,3,6-tri-O-benzyl-myo-inositol undergoes efficient kinetic resolutions mediated by Pseudomonas sp. lipases (PS-C, PS-IM) and CaLB (Novozym 435). Under the best conditions, the O-acylated L-enantiomorph was obtained in up to >99% ee with conversions of up to >49%. Differences in the immobilization support of the Pseudomonas sp. lipases had a marked effect on their resolution performance. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.005

文献信息

• Kinetic resolution of a precursor for myo-inositol phosphates under continuous flow conditions
  作者：Evelin A. Manoel、Karla C. Pais、Marcella C. Flores、Leandro Soter de M. e Miranda、Maria Alice Zarur Coelho、Alessandro B.C. Simas、Denise M.G. Freire、Rodrigo Octavio M.A. de Souza

  DOI：10.1016/j.molcatb.2012.11.006

  日期：2013.3

  In this work, we have investigated the biocatalytic continuous flow process with a packed-bed reactor for the kinetic resolution of (+/-)-1,3,6-tri-O-benzyl-rnyo-inositol ((+/-)-1) by alcoholysis using Novozym 435. Excellent conversions and stereselectivities were attained in short reaction time. We found that this enzymatic transformation under continuous flow in TBME with vinyl acetate (10:1 ratio with (+/-)-1) at 50 degrees C, with a 3 min-residence time secured the best results (50% conversion and ee(p) > 99%). The feasibility of a continuous operation of the Novozym 435-containing-packed-bed reactor over a longer period of time was demonstrated via a 9-cycle experiment wherein the lipase remained stable. (C) 2012 Elsevier B.V. All rights reserved.